Chem Test 2 (10/22)

Amines

ammonia that has 1,2, or all hydrogens replaced with carbon (R)

Amine Geometry

trigonal pyramidal 109.5

Amine 1 and 2 bonds

N-H bonds, hydrogen bond in pure solutions with other polar molecules like water

Amine 3 bond

N-C, dipole - dipole, covalent

Amine to Amine BP

1 and 2 have higher BP, because of H bonding, than (3) tertiary

Amine to alcohol BP

lower BP than alcohol of similar size because of lower polarity of N-H bonds compared to OH (alcohol)

Amine solubility

similar to alcohols due to ability to hydrogen bond with water, 1 and 2 more soluble because tertiary doesn’t have N-H bonds so less H bonding

Levels of solubility depending on number of carbons

C3> soluble, C4 somewhat, >C5 insoluble

key functional group in many pharmaceuticals

amines

how do amines work in the brain and body

responsible for physiological activity of neurotransmitters in the brain and other endogenous substances in the body

Alkaloids

naturally occurring compounds that contain amines, examples morphine, codeine, heroin, plant based can come from fugi, bacteria, animals

Bronsted-Lowry Acids in reactions

donate a proton (H+)

Bronsted-Lowry Bases

accept protons (H+)

Ammonia (base) and amines in water

amines will accept a proton from the ammonium ion (NH4+) and hydroxide (OH-)

are reactants or products favored in water

reactants

What happens when an amine reacts with an acid

a neutralization reaction forms and products are favored

accepts proton from water

Conjugate Acid

chemical substance formed when a base accepts a proton during Bronsted Lowry acid-base reaction

Conjugate Base

chemical substance left over after Bronsted Lowry acid donates a proton during chemical reaction

Amine salt solution

soluble in water due to ionic bonds , created when an acid donates a proton to a amine base

Salts

ionic compounds, soluble in water, bioavailable, in an aqueous environment like mucous membranes, blood, stomach; used in chemistry for pharmaceutics

Which is more soluble in water? Ionic compounds (salts) or polar covalent compound

ionic compound salts

Carbonyl

carbon double bonded to a oxygen (C=O)

Aldehyde Skeletal and General Structure

RCHO

Ketone Skeletal and General Structure

RCOR

Carboxylic Acid Skeletal and General Structure

RCOOH, RCO2H

Ester Skeletal and General Structure

RCOOR, RCO2R

Amide Skeletal and General Structure

RCONH2, RCONHR, RCOHNR2

Groups always on the end of a molecule (terminal)

Aldehydes, Carboxylic Acid

C=O in Aldehydes

permanent dipole, O has partial negative charge and C has a partial positive

Aldehyde Geometry

trigonal planer 120 degrees

Aldehyde boiling point

C=O is less polar than OH so they cannot hydrogen bond in pure solutions, lower boiling points than alcohols and amines

Aldehyde bonding

dipole-dipole and dispersion forces, can hydrogen bond with water in pure solutions, lower than alcohol

Aldehyde solubility

less soluble than alcohols, increasing carbons decreases solubility

Overal BP Ranking

amides> carboxylic acid> alcohols> amines> aldehydes> ester> ethers> HC

Aldehyde suffix

-al, drop “e“ of “ane”

Ketone Properties

very similar to aldehydes

Ketone Bonding

dipole-dipole, can H bond with water

Ketone BP

lower than alcohols, so close to aldehydes we won’t compare

Ketone solubility

fewer 3 C soluble, larger than 4 C are not

Ketone suffix

- one, replace “e“ of “ane“ with -one, always need locator number

How do carboxylic acids react in water/ in nuetral water

dissociate less, produce fewer H+ ions/ in neutral water it losses a hydrogen to water base and becomes carboxylate ion

Carboxylic Acids are _ _ Acids

weak, organic, weak, they donate a proton (H+)

Carboxylic acid physical properties

depend on the pH of the environment

Carboxylic Acid pH

around 7.4, slightly above neutral

Carboxylic acids will be in which form

carboxylate form

Carboxylic Acid neutral form

Carboxylic Acid carboxylate form

Carboxylic Acids BP

higher than alcohols

Carboxylic Acid Dimer

hydrogen bond in 2 places, strong H-bond with itself due to OH bond, held together by covalent bond sor intermolecular forces

Carboxylic Acid Solubility

more soluble than alcohols due to H bonding

Carboxylic Acid suffix

-oic, leave space between the parent and acid

Carboxylate suffix

-oate

Benzene + carboxylic acid

benzoic acid

Carboxylic Acid Derivative

esters, amides

Ester Bonding

dipole-dipole interactions, in pure solutions, weaker than alcohols or carboxylic acids, can H-bond in water

Ester BP

greater than alkenes lower than carbonyls and alcohol

Ester Solubility

soluble in water with less than 4 C

Ester smell

pleasant, fruity

Ester suffix

-oate, leave a space between the substituents and parent

Amine group location

must be directly attached to carbonyl carbon

Properties of amines vs. amides (organic bases)

amines

Properties of amines vs. amides (form ions at physiological pH)

amines

Properties of amines vs. amides (has some double bond character)

amides

Properties of amines vs. amides (influences shape of proteins)

amides

Amides 1/2 BP

higher than carboxylic acids and can form dimers

Amides 3 BP

lower than primary and secondary, bc no hydrogen for H bonding

Amide vs carboxylic acid form at room temp

amides are solid, carboxylic acids are liquid

Peptides and biomolecules are made from BLANK and connected by BLANK

amino acids, amide bonds - C (=O) - N -H -

Locator number for nitrogen R groups in amides

use “N”

Amide suffix

amide, hexanamide

Reactive sites of a molecule

functional groups

Organic reactions are

transformation of one functional group to another, changes number of c-c bonds, typically one is changed at a time

Biochemical reactions

happen inside of cells using enzymes and coenzymes

how are biochemical reactions done in a lab

synthesized using different chemical reagents and conditions like heat, reagents, catalysts, etc.

Compare biochemical and lab reactions

reactions and products are the same with different routes

number of Biochemical reaction enzyme classes

6, only 4 asked

enzyme suffix

-ase

Oxidation/reduction

oxidoreductases

Acyl Group transfers

transferases

Hydrolysis

hydrolases

hydration/dehydration

lyases

Oxidation-Reduction Reactions

reactant that gains electrons is reduced; reduction refers to a reduction in the charge of the ato, more electrons means more negative charge

Oxidation

increases charge, more positive, C-O bonds increased, C-H bonds decreased, C-C bond can also increase

Reduction

C-O bonds decrease, C-H bonds increase, more negative charge

Oxidizing Agent

loses oxygens, gains hydrogens, reactant that is reduced

Oxidizing agent symbol

[O]

Reducing agent

more oxygen, less hydrogen, reactant that is oxidized

Reducing Agent Symbol

[H]

Common Oxidizing Agents in a lab

NaOCl Bleach

O2 oxygen

H2O2 hydrogen peroxide

(Cr6+) Chromium VI

Common Oxidizing Agents biological

NAD+

FAD

Common reducing agents in a lab

hydrogen gas H2, sodium borohydride (NaBH4)

Commom reducing agents biological

NADH, FADH2

Alkane to alkene

Industrial Synthesis catalytic hydrogenation, needs a catalyst it start, hydrogen gas as a reducing agent, and a heavy metal like Pd or Pt, converts oil to fats

What makes trans fats

trans double-bonded, called hydrogenated or partially. hydrogenated

Oxidation of an alkane

succinate to fumarate,

c-c between 2 and 3 becomes an alkene,

FAD is coenzyme,

FAD →FADH2

Redox of C-C bonds

FADH2

Oxidaizing agent for C-C

FAD from vitamin B2

(oxidation)1* Alcohol →

aldehyde

(oxidation) aldehyde →

carboxylic acid